US8791303B2ActiveUtilityPatentIndex 38
Herbicides
Est. expiryJul 16, 2029(~3 yrs left)· nominal 20-yr term from priority
Inventors:FOLEY DANIEL JASONJEANMART STEPHANE ANDRÉ MARIELONGSTAFF ADRIANPARSONS ROBERT WILLIAMRUSSELL CLAIRE JANETTAYLOR JOHN BENJAMINWAILES JEFFREY STEVEN
C07D 285/06A01N 35/06A01N 35/10A01N 37/02A01N 37/34A01N 37/42A01N 41/10A01N 43/82C07C 49/657C07C 49/683C07C 49/697C07C 69/24C07C 69/63C07C 251/44C07C 255/56C07C 317/24C07C 2601/02C07C 2601/04C07C 2601/08C07C 2601/10C07C 2601/14C07C 2601/18C07C 2602/28
38
PatentIndex Score
2
Cited by
41
References
25
Claims
Abstract
Compounds of formula (I) are suitable for use as herbicides: wherein R is methyl, ethyl, vinyl, ethynyl or cyclopropyl, R 1 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, vinyl, propenyl, ethynyl, propynyl, halogen, or optionally substituted phenyl, R 2 is methyl, ethyl, vinyl, ethynyl or methoxy, R 3 and R 4 are hydrogen or together form a double bond, A is C 3 -C 7 cycloalkyl which is unsubstituted or substituted once or twice by C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyloxy, C 2 -C 6 alkenyl, ═O or ═N—R 10 , or A is cyclohexyl substituted once, at the 4-position, by one (C 3 -C 6 cycloalkyl)methoxy, C 3 -C 6 cycloalkyloxy, C 2 -C 5 alkenyl-CH 2 -oxy, or benzyloxy substituent, or A is decahydro-1-naphthyl or decahydro-2-naphthyl, or A is optionally substituted phenyl, and G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or a latentiating group.
Claims
exact text as granted — not AI-modifiedThe invention claimed is:
1. A compound of formula I
wherein
R is methyl, ethyl, vinyl, ethynyl or cyclopropyl,
R 1 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, vinyl, propenyl, ethynyl, propynyl, halogen, phenyl, or phenyl substituted by C 1 -C 4 alkyl, CF 3 , CF 2 Cl, CF 2 H, CCl 2 H, FCH 2 , ClCH 2 , BrCH 2 , CH 3 CHF, (CH 3 ) 2 CF, CF 3 CH 2 , CHF 2 CH 2 , C 1 -C 4 alkylsulfonyl, halogen, nitro or cyano,
R 2 is methyl, ethyl, vinyl, ethynyl or methoxy,
R 3 and R 4 are hydrogen or together form a double bond, and
A is C 3 -C 7 cycloalkyl which is unsubstituted or substituted once or twice by C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyloxy, C 2 -C 6 alkenyl, ═O or ═N—R 10 , where R 10 is hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy, or A is cyclohexyl substituted once, at the 4-position (calculated with respect to the cyclohexyl connection point), by one (C 3 -C 6 cycloalkyl)methoxy, C 3 -C 6 cycloalkyloxy, C 2 -C 5 alkenyl-CH 2 -oxy, benzyloxy, (monomethyl- or dimethyl-phenyl)methoxy, (monomethoxy- or dimethoxy-phenyl)methoxy or (monofluoro- or difluoro-phenyl)methoxy substituent,
or A is decahydro-1-naphthyl or decahydro-2-naphthyl,
or A is optionally substituted phenyl, and
G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or a latentiating group;
wherein, when G is a latentiating group, the latentiating group G is selected from the groups C 1 -C 8 alkyl, C 2 -C 8 haloalkyl, phenylC 1 -C 8 alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano or by nitro), heteroarylC 1 -C 8 alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano or by nitro), C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 alkynyl, C(X a )—R a , C(X b )—X c —R b , C(X d )—N(R c )—R d , —SO 2 —R e , —P(X e )(R f )—R 9 and CH 2 —X f —R h ;
wherein X a , X b , X c , X d , X e and X f are independently of each other oxygen or sulfur;
and wherein R a is H, C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 1 -C 10 aminoalkyl, C 1 -C 5 alkylamino(C 1 -C 5 )alkyl, C 2 -C 8 dialkylamino(C 1 -C 5 )alkyl, C 3 -C 7 cycloalkyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxy(C 1 -C 5 )alkyl, C 3 -C 5 alkenyloxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylthio(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfinyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfonyl(C 1 -C 5 )alkyl, C 2 -C 8 alkylideneaminoxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxycarbonyl(C 1 -C 5 )alkyl, aminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylaminocarbonyl(C 1 -C 5 )alkyl, C 2 -C 8 dialkylaminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonylamino(C 1 -C 5 )alkyl, N—(C 1 -C 5 )alkylcarbonyl-N—(C 1 -C 5 )alkylamino(C 1 -C 5 )alkyl, C 3 -C 6 -trialkylsilyl(C 1 -C 5 )alkyl, phenyl(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), heteroaryl(C 1 -C 5 )alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro;
R b is C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 18 alkynyl, C 2 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 2 -C 10 aminoalkyl, C 1 -C 5 alkylamino(C 1 -C 5 )alkyl, C 2 -C 8 dialkylamino(C 1 -C 5 )alkyl, C 3 -C 7 cycloalkyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxy(C 1 -C 5 )alkyl, C 3 -C 5 alkenyloxy(C 1 -C 5 )alkyl, C 3 -C 5 alkynyloxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylthio(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfinyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfonyl(C 1 -C 5 )alkyl, C 2 -C 8 alkylideneaminoxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxycarbonyl(C 1 -C 5 )alkyl, aminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylaminocarbonyl(C 1 -C 5 )alkyl, C 2 -C 8 dialkylaminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonylamino(C 1 -C 5 )alkyl, N—(C 1 -C 5 )alkylcarbonyl-N—(C 1 -C 5 )alkylamino(C 1 -C 5 )alkyl, C 3 -C 6 -trialkylsilyl(C 1 -C 5 )alkyl, phenyl(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), heteroarylC 1 -C 5 alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkyl-thio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), C 3 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro; and
R c and R d are each independently of each other hydrogen, C 1 -C 10 alkyl, C 3 -C 10 alkenyl, C 3 -C 10 alkynyl, C 2 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 1 -C 10 aminoalkyl, C 1 -C 5 alkylamino(C 1 -C 5 )alkyl, C 2 -C 8 dialkylamino(C 1 -C 5 )alkyl, C 3 -C 7 cycloalkyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxy(C 1 -C 5 )alkyl, C 3 -C 5 alkenyloxy(C 1 -C 5 )alkyl, C 3 -C 5 alkynyloxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylthio(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfinyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfonyl(C 1 -C 5 )alkyl, C 2 -C 8 alkylideneaminoxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxycarbonyl(C 1 -C 5 )alkyl, aminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylaminocarbonyl(C 1 -C 5 )alkyl, C 2 -C 8 dialkylaminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonylamino(C 1 -C 5 )alkyl, N—(C 1 -C 5 )alkylcarbonyl-N—(C 2 -C 5 )alkylaminoalkyl, C 3 -C 8 -trialkylsilyl(C 1 -C 5 )alkyl, phenyl(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), heteroaryl(C 1 -C 5 )alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, heteroaryl or heteroaryl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, heteroarylamino or heteroarylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, diheteroarylamino or diheteroarylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, phenylamino or phenylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro, diphenylamino or diphenylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro or C 3 -C 7 cycloalkylamino, di-C 3 -C 7 cycloalkylamino or C 3 -C 7 cycloalkoxy;
or R c and R d may join together to form a 3-7 membered ring, optionally containing one heteroatom selected from O or S; and
R e is C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 1 -C 10 aminoalkyl, C 1 -C 5 alkylamino(C 1 -C 5 )alkyl, C 2 -C 8 dialkylamino(C 1 -C 5 )alkyl, C 3 -C 7 cycloalkyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxy(C 1 -C 5 )alkyl, C 3 -C 5 alkenyloxy(C 1 -C 5 )alkyl, C 3 -C 5 alkynyloxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylthio(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfinyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfonyl(C 1 -C 5 )alkyl, C 2 -C 8 alkylideneaminoxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxycarbonyl(C 1 -C 5 )alkyl, aminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylaminocarbonyl(C 1 -C 5 )alkyl, C 2 -C 8 dialkylaminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonylamino(C 1 -C 5 )alkyl, N—(C 1 -C 5 )alkylcarbonyl-N—(C 1 -C 5 )alkylamino(C 1 -C 5 )alkyl, C 3 -C 6 -trialkylsilyl(C 1 -C 5 )alkyl, phenyl(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), heteroaryl(C 1 -C 5 )alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, heteroaryl or heteroaryl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro, heteroarylamino or heteroarylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro, diheteroarylamino or diheteroarylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, phenylamino or phenylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, diphenylamino or diphenylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, or C 3 -C 7 cycloalkylamino, diC 3 -C 7 cycloalkylamino, C 3 -C 7 cycloalkoxy, C 1 -C 10 alkoxy, C 1 -C 10 haloalkoxy, C 1 -C 5 alkylamino or C 2 -C 8 dialkylamino;
R f and R g are each independently of each other C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 alkoxy, C 1 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 1 -C 10 aminoalkyl, C 1 -C 5 alkylamino(C 1 -C 5 )alkyl, C 2 -C 8 dialkylamino(C 1 -C 5 )alkyl, C 3 -C 7 cycloalkyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxy(C 1 -C 5 )alkyl, C 3 -C 5 alkenyloxy(C 1 -C 5 )alkyl, C 3 -C 5 alkynyloxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylthio(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfinyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfonyl(C 1 -C 5 )alkyl, C 2 -C 8 alkylideneaminoxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxycarbonyl(C 1 -C 5 )alkyl, aminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylaminocarbonyl(C 1 -C 5 )alkyl, C 2 -C 8 dialkylaminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonylamino(C 1 -C 5 )alkyl, N—(C 1 -C 5 )alkylcarbonyl-N—(C 2 -C 5 )alkylaminoalkyl, C 3 -C 6 -trialkylsilyl(C 1 -C 5 )alkyl, phenyl(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), heteroaryl(C 1 -C 5 )alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, heteroaryl or heteroaryl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro, heteroarylamino or heteroarylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro, diheteroarylamino or diheteroarylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C r C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, phenylamino or phenylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, diphenylamino or diphenylamino substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, or C 3 -C 7 cycloalkylamino, diC 3 -C 7 cycloalkylamino, C 3 -C 7 cycloalkoxy, C 1 -C 10 haloalkoxy, C 1 -C 5 alkylamino or C 2 -C 8 dialkylamino, or benzyloxy or phenoxy, wherein the benzyl and phenyl groups may in turn be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro; and
R h is C 1 -C 10 alkyl, C 3 -C 10 alkenyl, C 3 -C 10 alkynyl, C 1 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 2 -C 10 aminoalkyl, C 1 -C 5 alkylamino(C 1 -C 5 )alkyl, C 2 -C 8 dialkylamino(C 1 -C 5 )alkyl, C 3 -C 7 cycloalkyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxy(C 1 -C 5 )alkyl, C 3 -C 5 alkenyloxy(C 1 -C 5 )alkyl, C 3 -C 5 alkynyloxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylthio(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfinyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylsulfonyl(C 1 -C 5 )alkyl, C 2 -C 8 alkylideneaminoxy(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkoxycarbonyl(C 1 -C 5 )alkyl, aminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylaminocarbonyl(C 1 -C 5 )alkyl, C 2 -C 8 dialkylaminocarbonyl(C 1 -C 5 )alkyl, C 1 -C 5 alkylcarbonylamino(C 1 -C 5 )alkyl, N—(C 1 -C 5 )alkylcarbonyl-N—(C 1 -C 5 )alkylamino(C 1 -C 5 )alkyl, C 3 -C 6 -trialkylsilyl(C 1 -C 5 )alkyl, phenyl(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano or by nitro), heteroaryl(C 1 -C 5 )alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano or by nitro), phenoxy(C 1 -C 5 )alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano or by nitro), heteroaryloxy(C 1 -C 5 )alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano or by nitro), C 3 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen or by nitro, or heteroaryl, or heteroaryl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro;
and wherein, when A is optionally substituted phenyl, then,
either:
(a) the compound of formula (I) is a compound of formula (IB):
wherein:
G is hydrogen;
R 2 is CH 3 or CH 3 O;
R 1 is CH 3 , CH 2 CH 3 , F, Cl, Br, CH 3 O, CH 3 CH 2 O, —CH═CH 2 , —CCH, phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2-nitrophenyl, 2-methylphenyl, 2-methanesulfonylphenyl, 2-cyanophenyl, 3-fluorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-nitrophenyl, 3-methylphenyl, 3-methanesulfonylphenyl, 3-cyanophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-difluoromethoxyphenyl, 2-fluoro-4-chlorophenyl, 3-fluoro-4-chlorophenyl, 2-chloro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-chlorophenyl, 3-chloro-4-fluorophenyl, 2-methyl-4-chlorophenyl, 4-trifluoromethylphenyl, 4-nitrophenyl, 4-methylphenyl, 4-methanesulfonylphenyl, or 4-cyanophenyl; and
A is of sub-formula (xv), (xvi), (xvii), (xviii), (xix), (xx) or (xxi):
(b) the compound is one of the following compounds A13, A15, A16, A18, A20, A21, A22, B7, B8, B9, B10, B11, B12, B13, B14, B15, B16, B17, B18 or B19, or is one of the following compounds C1 to C10:
2. Compound according to claim 1 , wherein
R is methyl, ethyl, vinyl, ethynyl or cyclopropyl,
R 1 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, vinyl, propenyl, ethynyl, propynyl, halogen, phenyl, or phenyl substituted by C 1 -C 4 alkyl, CF 3 , CF 2 Cl, CF 2 H, CCl 2 H, FCH 2 , ClCH 2 , BrCH 2 , CH 3 CHF, (CH 3 ) 2 CF, CF 3 CH 2 , CHF 2 CH 2 , C 1 -C 4 alkylsulfonyl, halogen, nitro or cyano,
R 2 is methyl, ethyl, vinyl, ethynyl or methoxy,
R 3 and R 4 are hydrogen or together form a double bond,
A is C 3 -C 7 cycloalkyl which is unsubstituted or substituted once or twice by C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyloxy, C 2 -C 6 alkenyl, ═O or ═N—R 10 , where R 10 is hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy,
or A is optionally substituted phenyl as defined in claim 1 , and
G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium, or latentiating group,
wherein the latentiating group is as defined in claim 1 .
3. Compound according to claim 2 , wherein R 1 is C 1 -C 4 alkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, halogen, phenyl, or phenyl substituted by C 1 -C 4 alkyl, CF 3 , CF 2 C 1 , CF 2 H, CCl 2 H, FCH 2 , ClCH 2 , BrCH 2 , CH 3 CHF, (CH 3 ) 2 CF, CF 3 CH 2 , CHF 2 CH 2 , C 1 -C 4 alkylsulfonyl, halogen, nitro or cyano.
4. Compound according to claim 1 , wherein R 1 is C 1 -C 4 alkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, halogen, phenyl, or phenyl substituted by C 1 -C 4 alkyl, CF 3 , CF 2 C 1 , CF 2 H, CCl 2 H, FCH 2 , ClCH 2 , BrCH 2 , CH 3 CHF, (CH 3 ) 2 CF, CF 3 CH 2 , CHF 2 CH 2 , C 1 -C 4 alkylsulfonyl, halogen, nitro or cyano.
5. Compound according to claim 4 , wherein R 1 is C 1 -C 4 alkyl or halogen.
6. Compound according to claim 1 , wherein R 2 is methyl.
7. Compound according to claim 1 , wherein R 3 and R 4 are hydrogen.
8. Compound according to claim 1 , wherein A is C 3 -C 7 -cycloalkyl which is unsubstituted or substituted once or twice by C 1 -C 4 alkyl, C 1 -C 6 alkylcarbonyloxy, C 4 -C 6 alkenyl, ═O or ═N—R 10 , where R 10 is hydroxyl or C 1 -C 4 alkoxy.
9. Compound according to claim 1 , wherein G is hydrogen or an agriculturally acceptable metal, sulfonium or ammonium group, or a latentiating group of the formula C(X a )—R a or C(X b )—X c —R b , wherein X a and X b are independently of each other oxygen or sulfur, and R a and R b are as defined in claim 1 .
10. Compound according to claim 1 , wherein G is hydrogen or an agriculturally acceptable metal, sulfonium or ammonium group, or a latentiating group of the formula C(X a )—R a or C(X b )—X c —R b , wherein X a and X b are independently of each other oxygen or sulfur, and R a is hydrogen or C 1 -C 18 alkyl and R b is C 1 -C 18 alkyl.
11. Compound according to claim 1 , wherein
R 1 is C 1 -C 6 alkyl or halogen,
R 2 is methyl,
R 3 and R 4 are hydrogen or together form a double bond, and
A is C 3 -C 7 -cycloalkyl which is unsubstituted or substituted once or twice by C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, C 2 -C 6 alkenyl, ═O or ═N—R 10 , where R 10 is hydroxyl or C 1 -C 6 alkoxy, and
G is hydrogen or a latentiating group.
12. Compound according to claim 11 , wherein
R 1 is methyl or bromo,
R 2 is methyl,
R 3 and R 4 are hydrogen, and
A is C 5 - or C 6 -cycloalkyl which is unsubstituted or substituted once or twice by methyl, propenyl, methylcarbonyloxy, ═O or ═N—R 10 , where R 10 is hydroxyl or methoxy, and
G is hydrogen or pivaloyl.
13. Compound according to claim 1 , wherein A is optionally substituted phenyl, and either:
(a) the compound of formula (I) is a compound of formula (IB):
wherein:
G is hydrogen;
R 2 is CH 3 or CH 3 O;
R 1 is CH 3 , CH 2 CH 3 , F, Cl, Br, CH 3 O, CH 3 CH 2 O, —CH═CH 2 , —CCH, phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2-nitrophenyl, 2-methylphenyl, 2-methanesulfonylphenyl, 2-cyanophenyl, 3-fluorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-nitrophenyl, 3-methylphenyl, 3-methanesulfonylphenyl, 3-cyanophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-difluoromethoxyphenyl, 2-fluoro-4-chlorophenyl, 3-fluoro-4-chlorophenyl, 2-chloro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-chlorophenyl, 3-chloro-4-fluorophenyl, 2-methyl-4-chlorophenyl, 4-trifluoromethylphenyl, 4-nitrophenyl, 4-methylphenyl, 4-methanesulfonylphenyl, or 4-cyanophenyl; and
A is of sub-formula (xv), (xvi), (xvii), (xviii), (xix), (xx) or (xxi):
(b) the compound is one of the following compounds A13, A15, A16, A18, A20, A21, A22, B7, B8, B9, B10, B11, B12, B13, B14, B15, B16, B17, B18 or B19:
14. Compound according to claim 1 , which is a compound of formula (IA):
wherein G is hydrogen;
R 2 is CH 3 or CH 3 O;
R 1 is CH 3 , CH 2 CH 3 , F, Cl, Br, CH 3 O, CH 3 CH 2 O, —CH═CH 2 , —CCH, phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2-nitrophenyl, 2-methylphenyl, 2-methanesulfonylphenyl, 2-cyanophenyl, 3-fluorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-nitrophenyl, 3-methylphenyl, 3-methanesulfonylphenyl, 3-cyanophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-difluoromethoxyphenyl, 2-fluoro-4-chlorophenyl, 3-fluoro-4-chlorophenyl, 2-chloro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-chlorophenyl, 3-chloro-4-fluorophenyl, 2-methyl-4-chlorophenyl, 4-trifluoromethylphenyl, 4-nitrophenyl, 4-methylphenyl, 4-methanesulfonylphenyl, or 4-cyanophenyl; and
A is of sub-formula (i), (ii), (iii), (iv), (v), (vi), (vii), (viii), (ix), (x), (xi), (xii), (xiii) or (xiv):
15. Compound according to claim 14 , wherein A is of sub-formula (iii), (iv), (vi) or (vii).
16. Compound according to claim 1 , which is a compound of formula (IC):
wherein G is hydrogen;
R 2 is CH 3 or CH 3 O;
R 1 is CH 3 , CH 2 CH 3 , F, Cl, Br, CH 3 O, CH 3 CH 2 O, —CH═CH 2 , —CCH, phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2-nitrophenyl, 2-methylphenyl, 2-methanesulfonylphenyl, 2-cyanophenyl, 3-fluorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-nitrophenyl, 3-methylphenyl, 3-methanesulfonylphenyl, 3-cyanophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-difluoromethoxyphenyl, 2-fluoro-4-chlorophenyl, 3-fluoro-4-chlorophenyl, 2-chloro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-chlorophenyl, 3-chloro-4-fluorophenyl, 2-methyl-4-chlorophenyl, 4-trifluoromethylphenyl, 4-nitrophenyl, 4-methylphenyl, 4-methanesulfonylphenyl, or 4-cyanophenyl; and
A is of sub-formula (6b), (6c), (6d), (6e), (6f), (6g), (6h), or (6i):
17. Compound according to claim 14 , wherein R 1 is CH 3 , CH 2 CH 3 , F, Cl, or Br.
18. Compound according to claim 14 , wherein R 2 is CH 3 .
19. Compound according to claim 1 , which is one of Compounds A1 to A9, A11 to A24, A38, or B1 to B19, as defined by the structures shown below:
20. Compound according to claim 1 , which is one of Compounds A25 to A37, A39 to A47, B20 to B28, or C1 to C10, as defined by the structures shown below:
21. A herbicidal composition, which comprises a herbicidally effective amount of a compound of formula I as defined in claim 1 .
22. A herbicidal composition according to claim 21 , which comprises a herbicidally effective amount of a compound of formula I as defined in claim 1 , and optionally a further herbicide as mixture partner for the compound of formula I, or optionally a safener, or both.
23. A herbicidal composition according to claim 22 , which comprises a herbicidally effective amount of a compound of formula I as defined in any claim 1 , a safener, and optionally a further herbicide as mixture partner for the compound of formula I,
wherein the safener is benoxacor, cloquintocet-mexyl, cyprosulfamide, mefenpyr-diethyl or N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide.
24. A method of controlling grasses and weeds in crops of useful plants, which comprises applying a herbicidally effective amount of a compound of formula I as defined in claim 1 , to the plants or to the locus thereof.
25. A method according to claim 24 , wherein the crops of useful plants are wheat, barley, corn or soybean.Cited by (0)
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